(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 178432815, compound

HRID 1630107Notes

Reaction equation

HRID 1630107 reaction equation
Cl.[CH3:2][C:3]1[NH:4][CH:5]=[C:6]([CH2:8][C:9]([OH:11])=O)[N:7]=1.[NH2:12][C@@H:13]([CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)=[O:15]>>[CH2:33]([O:32][CH2:31][C@H:13]([NH:12][C:9](=[O:11])[CH2:8][C:6]1[N:7]=[C:3]([CH3:2])[NH:4][CH:5]=1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)=[O:15])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 178432817HCID 178432817, compound

Product 1

HCID 178432815HCID 178432815, compoundYield 7%

Procedure

Proceeding as in Example 1, but substituting 2-(2-methyl-1H-imidazol-4-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 162, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(2-methyl-1H-imidazol-4-yl)acetamido)propanamide (52 mg, 7%). 1H-NMR (400 MHz, DMSO-D6): σ 10.19 (s, 1H), 8.40-8.36 (m, 2H), 7.61 (d, 2H), 7.32-7.18 (m, 6H), 7.04-6.97 (m, 3H), 6.74 (br s, 1H), 4.69-4.64 (m, 1H), 4.52 (s, 2H), 3.67-3.54 (m, 4H), 2.20 (s, 3H). MS (EI) for C28H27FN4O4. found 503.2 (MH+).

Sources & evidence

ORD record
ord-d8300471987646e88abb09d73e585be9
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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